Trihalogenated ms-benzdianthrones



Patented May '13, 1930 Um'rso STATES PATENT!v OFFICE MAX l ALBERT KUNZ,OF MANNHEIM, SWITZERLAND, AND KARL KOBERLE, OF LUD-WIGSHAFEN-ON-THE-RHINE, GERMANY, ASSIGNORS TO GENERAL ANILINE WORKS,INC., OF NEW YORK, N. Y., A CORPORATION OF DELAWARE TR-IHALOGENATEDMS-BENZDIANTHRONES Ho Drawing. Original application filed June 16, 1927,Serial No. 199,421, and in Germany March 15, 1926. Divided and thisapplication filed February 2, 1928. Serial No. 251,455.

This application contains subject matter which has been divided outfromour copending application for patent, Ser. No. 199,421, filed June16, 1927.

We have found that by treating msbenzdianthrone and its derivatives withhalogen or substances liberating halogen, at atmospheric pressure andpreferably in the presence of a halogen transporter, halogen derivativesare produced, the tinctorial properties of which meet all requirementsof practice. In the manner described more or less highly halogenatedderivatives can be obtained.

The most valuable products obtainable according to the present inventionare the trihalogen derivatives.

The following examples will further illustrate how our invention may becarried out in practice, but the invention is not limited to theseexamples. The parts are by weight.

E aample 1 from which the dibrom-ms-benzdianthrone corresponding to theformula ll can be easily obtained, for instance by precipitation from asolution invconcentrated sulfuric acid. The new coloring matterdissolves with a blue color in concentrated sulfuric acid andcrystallizes from benzene in orange-yellow needles. Cotton is dyed fromthe green vat strong yellow shades.

E mample 2 100 parts of ms-benzdianthrone and 5 parts of iodine aredissolved in 750 parts of nitrobenzene. 200 arts of bromine are added tothe solution, rop by drop, while stirring at about 100 C. As soon as allof the bromine has been added, the temperature is slowly raised to about150160 C. and the mixture maintained at this temperature for four hours.After cooling down, the precipitate is filtered off by suction. A brownish-yellow powder is thus obtained, which when recrystallized fromnitrobenzene gives brownish-yellow needles of tribrom-msbenzdianthrone.This substance dissolves in concentrated sulfuric acid with a bluishgreen color, and gives very strong goldenyellow shades on cotton.

Example 3 150 parts of sulfuryl chlorid are added at C. while stirringto a solution of 100 parts of ms-benzdianthrone in 400 to 500 parts ofnitrobenzene to which about 5 parts of iodine have been added. Themixture is stirred for 6 hours at this temperature, allowed to cool,

. and filtered with suction. The remainder of the reaction product canbe isolated from the filtered liquid by driving oil the nitrobenzene ourhands. a a

' MAX ALBERT KUNZ.

URL KOBERLE.

2 CERTIFICATE OF CORRECTION.

Patent No. 1,758,841. Granted May 13, 1930, m

MAX ALBERT KUNZ ET AL. It is hereby certified that error appears in theabove numbered patent requiring correction as follows: In the grant andin the heading to the printed specificationthe residence of the firstnamed patentee was erroneously written and printed as "Mannheim,Switzerland", whereas said residenoe should have been written andprinted as Mannheim, Germany; and that the said Letters Patent should beread with this correction therein that the same may conform to therecord of the case in thevPatent Office.

Signed and sealed this 5th day of August, D. 1930.

Win. A. Kinnan, (Seal) Acting Commissioner of Patents.

